WO2022109360A1 - Novel spiropyrrolidine derived antiviral agents - Google Patents
Novel spiropyrrolidine derived antiviral agents Download PDFInfo
- Publication number
- WO2022109360A1 WO2022109360A1 PCT/US2021/060243 US2021060243W WO2022109360A1 WO 2022109360 A1 WO2022109360 A1 WO 2022109360A1 US 2021060243 W US2021060243 W US 2021060243W WO 2022109360 A1 WO2022109360 A1 WO 2022109360A1
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- WO
- WIPO (PCT)
- Prior art keywords
- optionally substituted
- compound
- alkyl
- pharmaceutically acceptable
- cycloalkyl
- Prior art date
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- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000009256 replacement therapy Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 206010041232 sneezing Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- SOMOOKYLVGXVML-UHFFFAOYSA-M sodium 3-[3-tert-butylsulfanyl-1-[[4-(6-ethoxypyridin-3-yl)phenyl]methyl]-5-[(5-ethylpyridin-2-yl)methoxy]indol-2-yl]-2,2-dimethylpropanoate Chemical compound C(C)(C)(C)SC1=C(N(C2=CC=C(C=C12)OCC1=NC=C(C=C1)CC)CC1=CC=C(C=C1)C=1C=NC(=CC=1)OCC)CC(C(=O)[O-])(C)C.[Na+] SOMOOKYLVGXVML-UHFFFAOYSA-M 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- LZCVVMQABORALM-UHFFFAOYSA-N spiro[2.5]octyl Chemical group [CH]1CC11CCCCC1 LZCVVMQABORALM-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 229940021747 therapeutic vaccine Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 239000002750 tryptase inhibitor Substances 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229960004764 zafirlukast Drugs 0.000 description 1
- MWLSOWXNZPKENC-UHFFFAOYSA-N zileuton Chemical compound C1=CC=C2SC(C(N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229940052267 zyflo Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP21895733.0A EP4247387A1 (en) | 2020-11-23 | 2021-11-22 | Novel spiropyrrolidine derived antiviral agents |
CA3202764A CA3202764A1 (en) | 2020-11-23 | 2021-11-22 | Novel spiropyrrolidine derived antiviral agents |
AU2021383832A AU2021383832A1 (en) | 2020-11-23 | 2021-11-22 | Novel spiropyrrolidine derived antiviral agents |
CN202180084565.0A CN116829571A (en) | 2020-11-23 | 2021-11-22 | Novel spiral pyrrolidine derived antiviral drugs |
KR1020237020685A KR20230124583A (en) | 2020-11-23 | 2021-11-22 | Novel spiropyrrolidine-derived antiviral agent |
JP2023530256A JP2024500286A (en) | 2020-11-23 | 2021-11-22 | Novel spiropyrrolidine-derived antiviral agent |
IL302990A IL302990A (en) | 2020-11-23 | 2021-11-22 | Novel spiropyrrolidine derived antiviral agents |
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US202063117184P | 2020-11-23 | 2020-11-23 | |
US63/117,184 | 2020-11-23 |
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WO2022109360A1 true WO2022109360A1 (en) | 2022-05-27 |
Family
ID=81656811
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---|---|---|---|
PCT/US2021/060243 WO2022109360A1 (en) | 2020-11-23 | 2021-11-22 | Novel spiropyrrolidine derived antiviral agents |
Country Status (9)
Country | Link |
---|---|
US (1) | US20220162231A1 (en) |
EP (1) | EP4247387A1 (en) |
JP (1) | JP2024500286A (en) |
KR (1) | KR20230124583A (en) |
CN (1) | CN116829571A (en) |
AU (1) | AU2021383832A1 (en) |
CA (1) | CA3202764A1 (en) |
IL (1) | IL302990A (en) |
WO (1) | WO2022109360A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115894504A (en) * | 2022-10-21 | 2023-04-04 | 深圳信立泰药业股份有限公司 | Coronavirus 3CL protease inhibitor and application thereof |
WO2023109926A1 (en) * | 2021-12-17 | 2023-06-22 | 南京药石科技股份有限公司 | Spirooxindole compound and use thereof in preparation of protease inhibitor as antiviral drug |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11912714B2 (en) | 2021-11-12 | 2024-02-27 | Enanta Pharmaceuticals, Inc. | Spiropyrrolidine derived antiviral agents |
WO2023086400A1 (en) | 2021-11-12 | 2023-05-19 | Enanta Pharmaceuticals, Inc. | Novel spiropyrrolidine derived antiviral agents |
WO2023086350A1 (en) * | 2021-11-12 | 2023-05-19 | Enanta Pharmaceuticals, Inc. | Alkyne-containing antiviral agents |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012099454A1 (en) * | 2011-01-21 | 2012-07-26 | Universiti Sains Malaysia | Curcumin compounds and their preparations thereof |
-
2021
- 2021-11-22 CN CN202180084565.0A patent/CN116829571A/en active Pending
- 2021-11-22 KR KR1020237020685A patent/KR20230124583A/en unknown
- 2021-11-22 IL IL302990A patent/IL302990A/en unknown
- 2021-11-22 CA CA3202764A patent/CA3202764A1/en active Pending
- 2021-11-22 US US17/531,844 patent/US20220162231A1/en active Pending
- 2021-11-22 EP EP21895733.0A patent/EP4247387A1/en active Pending
- 2021-11-22 JP JP2023530256A patent/JP2024500286A/en active Pending
- 2021-11-22 WO PCT/US2021/060243 patent/WO2022109360A1/en active Application Filing
- 2021-11-22 AU AU2021383832A patent/AU2021383832A1/en active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012099454A1 (en) * | 2011-01-21 | 2012-07-26 | Universiti Sains Malaysia | Curcumin compounds and their preparations thereof |
Non-Patent Citations (2)
Title |
---|
DATABASE PUBCHEM SUBSTANCE 25 May 2018 (2018-05-25), ANONYMOUS : "SID 367622864", XP055939757, retrieved from PUBCHEM Database accession no. 367622864 * |
ZHOU LI-MING, QU REN-YU, YANG GUANG-FU: "An overview of spirooxindole as a promising scaffold for novel drug discovery", EXPERT OPINION ON DRUG DISCOVERY, INFORMA HEALTHCARE, LONDON, GB, vol. 15, no. 5, 3 May 2020 (2020-05-03), London, GB , pages 603 - 625, XP055939765, ISSN: 1746-0441, DOI: 10.1080/17460441.2020.1733526 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023109926A1 (en) * | 2021-12-17 | 2023-06-22 | 南京药石科技股份有限公司 | Spirooxindole compound and use thereof in preparation of protease inhibitor as antiviral drug |
CN115894504A (en) * | 2022-10-21 | 2023-04-04 | 深圳信立泰药业股份有限公司 | Coronavirus 3CL protease inhibitor and application thereof |
Also Published As
Publication number | Publication date |
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CA3202764A1 (en) | 2022-05-27 |
AU2021383832A1 (en) | 2023-06-22 |
IL302990A (en) | 2023-07-01 |
KR20230124583A (en) | 2023-08-25 |
EP4247387A1 (en) | 2023-09-27 |
US20220162231A1 (en) | 2022-05-26 |
CN116829571A (en) | 2023-09-29 |
JP2024500286A (en) | 2024-01-09 |
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